Imidazole → 3-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylcyclobutanecarboxamide

HRID 1966165Notes

Reaction equation

HRID 1966165 reaction equation
[OH:1][CH:2]1[CH2:5][CH:4]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])[CH2:3]1.[C:12]([Si:16](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:15])([CH3:14])[CH3:13].N1C=CN=C1>CN(C=O)C.ClCCl>[Si:16]([O:1][CH:2]1[CH2:5][CH:4]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])[CH2:3]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 186915573-hydroxy-N-methoxy-N-methylcyclobutanecarboxamide

Product 1

HCID 866343493-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylcyclobutanecarboxamideYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Into a solution of 3-hydroxy-N-methoxy-N-methylcyclobutanecarboxamide (0.6 g, 0.004 mol in DMF (10 mL) was added tert-butylchlorodiphenylsilane (3 mL, 0.01 mol), followed by 1H-imidazole (1 g, 0.02 mol). The mixture was stirred at rt over night. The reaction was diluted with dichloromethane and washed with sat. NaHCO3, water and brine. The organic layers were dried over MgSO4, concentrated and purified with Combiflash (silica gel, 0-30% EtOAc/Hex) to give the desired product (0.7 g, 50%) as cis- and trans-isomer mixtures. LCMS calculated for C23H32NO3Si(M+H)+: 398.2. Found: 398.1.

Workup

  1. washwashed with sat. NaHCO3, water and brine
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. custompurified with Combiflash (silica gel, 0-30% EtOAc/Hex)

Sources & evidence

ORD record
ord-53c1818f9999401197c2d1cdccaf2417
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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